I've been Windows-free for nearly four years now; breaking the addiction can be hard, but for me has been worthwhile.
File sharing generally isn't a problem; while Linux can't support the most recent Windows file sharing systems, Windows itself seems quite happy dealing with the version of Samba available under Linux.
Printer support is, admittedly, more hit-or-miss.
Not sure about Tomcat; if you're talking about the Java JSP stuff, that shouldn't be a problem...
OpenOffice.org is not as pretty as Office, but is compatible to an extent, and can do much of the same work. It can read and write at least older .doc files. (And honestly, it's a bad idea to allow your personal or business documents to be locked up in proprietary file formats at all...)
Well, OpenOffice.org has some ability to edit PDF files, and there are a few other editors out there. You could always just purchase Adobe Acrobat for Linux...
I know what you mean; nobody I talk to seems to like the complexity of modern image manipulation software (even on Windows; my brother insists on using an archaic photo editor on Windows, because he can't stand any modern alternatives). There are several small paint programs around, but I think you'll find they all have their own quirks.
In the end, moving to a new operating system means getting used to a new set of tools. You can pretty much do all the same stuff in Windows and in Linux, but you can't always do it in the same way or with the same company's products. You just have to invest the time and effort necessary to overcome the differences...